Triphenylphosphine → HCID 68903790, compound

HRID 1785731Notes

Reaction equation

HRID 1785731 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:27]([F:30])([F:29])[F:28])=[C:10]([CH2:14][O:15][CH:16]3[CH2:19][N:18]([C:20]([NH:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17]3)[CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[S:31]1[CH:35]=[CH:34][CH:33]=[C:32]1B(O)O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)(O)[O-].[Na+]>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[S:31]1[CH:35]=[CH:34][CH:33]=[C:32]1[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:27]([F:29])([F:30])[F:28])=[C:10]([CH2:14][O:15][CH:16]3[CH2:19][N:18]([C:20]([NH:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:17]3)[CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 27339602-Thiopheneboronic acidHCID 68903769HCID 68903769, compound

Product 1

HCID 68903790HCID 68903790, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of aryl iodide (191) (100 mg, 0.19 mmol), 2-thiopheneboronic acid (48 mg, 0.38 mmol), palladium acetate (4 mg, 0.019 mmol) and triphenylphosphine (10 mg, 0.38 mmol) in tetrahydrofuran (10 mL) was added sodium bicarbonate (10 mL, saturated aqueous). The reaction mixture was heated to reflux (65° C.) for 4 h, cooled, filtered and partitioned between water (20 mL) and ethyl acetate (20 mL). The organic phase was separated and washed with brine (20 mL), dried (Na2SO4), filtered and the solvent removed under reduced pressure to afford the crude product, as a brown oil. Purification by silica gel chromatography (20% ethyl acetate/iso-hexane eluant) gave the title compound (193) as a brown solid (67.2 mg, 73% yield).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperaturecooled
  3. filtrationfiltered
  4. custompartitioned between water (20 mL) and ethyl acetate (20 mL)
  5. customThe organic phase was separated
  6. washwashed with brine (20 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customthe solvent removed under reduced pressure
  10. customto afford the crude product
  11. customPurification by silica gel chromatography (20% ethyl acetate/iso-hexane eluant)

Sources & evidence

ORD record
ord-0cd42dda05e64188b4bc8d4b43d19fc1
Source dataset
uspto-grants-2009_03
Patent number
US07504522B2

Reaction notes

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